(E)-3-(甲基苯基氨基)-2-丙烯醛 | 34900-01-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: (E)-3-(甲基苯基氨基)-2-丙烯醛
• 英文名称: 3-(N-methyl-N-phenylamino)acrolein
• 英文别名: N-methyl-N-phenylaminoacrolein；3t-(N-methyl-anilino)-propenal；3-N-methyl-N-phenylaminoacrolein；3-(Methyl(phenyl)amino)acrylaldehyde；(E)-3-(N-methylanilino)prop-2-enal
• CAS: 34900-01-1
• 化学式: C₁₀H₁₁NO
• 分子量: 161.203
• InChiKey: YLMOTKLYENPQLK-VMPITWQZSA-N

物化性质

• 熔点：
  40-43°C
• 沸点：
  255.6±32.0 °C(Predicted)
• 密度：
  1.064±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2922399090

反应信息

• 作为反应物：
  描述：

  (E)-3-(甲基苯基氨基)-2-丙烯醛 在 manganese(IV) oxide 、 氯化锆(IV) 作用下， 以 乙醇 为溶剂， 反应 0.58h， 生成 2-[(E)-2-(methylphenylamino)ethenyl]-1-phenyl-1H-benzoimidazole-5-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Analogues of AKT (Protein Kinase B) Inhibitor-IV

  摘要：

  Inhibitors of the PI3-kinase/AKT (protein kinase B) pathway are under investigation as anticancer and antiviral agents. The benzimidazole derivative AKT inhibitor-IV (ChemBridge 5233705) affects this pathway and exhibits potent anticancer and antiviral activity. To probe its biological activity, we synthesized AKT inhibitor-IV and 21 analogues using a novel six-step route based on ZrCl4-catalyzed cyclization of 1,2-arylenediamines with alpha,beta-unsaturated aldehydes. We examined effects on viability of HeLa carcinoma cells, viability of normal human cells (NHBE), replication of recombinant parainfluenza virus 5 (PIV5) in HeLa cells, and replication of the intracellular bacterium Mycobacterium fortuitum in HeLa cells. Replacement of the benzimidazole N-ethyl substitutent of AKT inhibitor-IV with N-hexyl and N-dodecyl groups enhanced antiviral activity and cytotoxicity against the cancer cell line, but these compounds showed substantially lower toxicity (from 6-fold to >20-fold) against NHBE cells and no effect on M. fortuitum, suggesting inhibition of one or more host protein(s) required for proliferation of cancer cells and PIV5. The key structural elements identified here may facilitate identification of targets of this highly biologically active scaffold.

  DOI：

  10.1021/jm100912b
• 作为产物：
  描述：

  乙烯基正丁醚 、 N-甲基甲酰苯胺 在 三光气 、 sodium hydroxide 作用下， 以 氯苯 、 水 为溶剂， 以88%的产率得到(E)-3-(甲基苯基氨基)-2-丙烯醛
  参考文献：
  名称：

  Process for the synthesis of N-methyl-N-phenylaminoacrolein

  摘要：

  公开了一种制备式(I)的N-甲基-N-苯基氨基丙烯醛的方法，该方法包括反应N-甲基甲酰苯胺和式(III)的烷基乙烯醚，其中R为C3-C4烷基，其特征在于在二恶烷、乙腈和/或氯化苯等溶剂中，在光气、二光气或三光气的存在下，进行N-甲基甲酰苯胺和式(III)的烷基乙烯醚之间的反应。

  公开号：

  EP1477474A1

文献信息

• NUCLEIC ACID BINDING DYES AND USES THEREFOR
  申请人：McDougall Mark

  公开号：US20100233710A1

  公开（公告）日：2010-09-16

  The invention provides novel compounds and compositions of Formulas I and II, as well as methods of using them. The compounds can be used, for example, to quantify an amount of double stranded DNA in a sample subjected to nucleic acid amplification, or for real time monitoring of a nucleic acid amplification reaction. The compounds can be provided in a kit, for example, with other reagents and instructions for using the compounds and reagents.

  这项发明提供了Formula I和Formula II的新化合物和组合物，以及使用它们的方法。这些化合物可以用于例如，在经过核酸扩增的样本中定量双链DNA的数量，或者用于实时监测核酸扩增反应。这些化合物可以作为一种试剂盒的一部分提供，例如，与其他试剂和使用这些化合物和试剂的说明书一起。
• Acetylene mit Elektronendonator und Elektronenakzeptorgruppen
  作者：H.-J. Gais、K. Hafner、M. Neuenschwander

  DOI：10.1002/hlca.19690520845

  日期：——

  Acetylenes having both electrondonating and electronaccepting groups (1) may be obtained in good yield from the correspondingly substituted olefines via bromination and elimination of HBr. The reaction of the acetylene aldehyde 1a with proton acids yields, after rearrangement of the primary adducts, the β-substituted acrylamides. Addition of nucleophiles leads to the β-disubstituted α.β-unsaturated

  可以通过溴化和消除HBr，从相应取代的烯烃以高收率获得同时具有给电子基团和电子接受基团（1）的乙炔。乙炔醛1a与质子酸的反应在伯加合物重排后产生β-取代的丙烯酰胺。亲核试剂的加入导致β-二取代的α.β-不饱和羰基化合物。用肼得到吡唑和吡唑啉酮。乙炔1经历[2 + 2]-，[2 + 3]-和[2 + 4]-环加成反应。
• Synthesis, crystal studies and in vivo anti-hyperlipidemic activities of indole derivatives containing fluvastatin nucleus
  作者：Veerendra Kumar A. Kalalbandi、J. Seetharamappa、Umesha Katrahalli

  DOI：10.1039/c5ra02908b

  日期：——

  synthesized some indole derivatives containing a fluvastatin nucleus by methanol mediated Claisen–Schmidt aldol condensation reaction. The newly synthesized molecules are characterized by FT-IR, 1H NMR, 13C NMR and LCMS spectral analyses. The structural parameters of 5b, 5c, 5g and 5h have been elucidated by X-ray diffraction studies. In vivo antihyperlipidemic activity and histopathological studies of all the

  为制备更好的氟伐他汀类似物来治疗高脂血症的努力的一部分，我们已经通过甲醇介导的Claisen-Schmidt醛醇缩合反应合成了一些含有氟伐他汀核的吲哚衍生物。通过FT-IR，1 H NMR，13 C NMR和LCMS光谱分析对新合成的分子进行表征。通过X射线衍射研究阐明了5b，5c，5g和5h的结构参数。已经研究了所有化合物的体内抗高血脂活性和组织病理学研究。在5a–l中，化合物5c和5i除血清高密度脂蛋白水平升高外，血清总胆固醇，甘油三酸酯，低密度脂蛋白和极低密度脂蛋白显着降低。与标准氟伐他汀药物相比，化合物5c和5i表现出明显的细胞质脂肪浸润以及颗粒变性。可以想象，药物类似物的合成可以产生更有效的治疗效果。另外，已经研究了最有效的降血脂药5c与人血清白蛋白HSA之间的相互作用。化合物5c可以主要通过以下方式与HSA可逆结合 一种涉及形成络合物的机理，其中氢键和疏水相互作用都是主要作用力。
• Processes for the synthesis of 3-disubstituted aminoacroleins
  申请人：Sandoz Ltd.

  公开号：US05118853A1

  公开（公告）日：1992-06-02

  Process for the synthesis of compounds of the formula ##STR1## comprising the steps of (i) reacting a compound of the formula ##STR2## with oxalyl chloride or oxalyl bromide to form the corresponding compound of the formula ##STR3## (ii) reacting said compound of the formula ##STR4## with a compound of the formula ##STR5## to form the corresponding compound of the formula ##STR6## (iii) hydrolyzing said compound of the formula ##STR7## to obtain the corresponding compound of the formula ##STR8## the use of the compounds of the formula ##STR9## for the synthesis of the compounds of the formula ##STR10## and the use of the intermediates of Formula VII for the direct synthesis of the compounds of Formula II, wherein R.sub.1 is C.sub.1-3 alkyl, phenyl or phenyl substituted by 1 to 3 substituents each of which is independently C.sub.1-3 alkyl, C.sub.1-3 alkoxy, fluoro, chloro, bromo or nitro (maximum of two nitro groups), R.sub.1b is phenyl or phenyl substituted by 1 to 3 substituents each of which is independently C.sub.1-3 alkyl, C.sub.1-3 alkoxy, fluoro, chloro, bromo or nitro (maximum of two nitro groups), R.sub.2 is C.sub.1-3 alkyl, one of R.sub.3 and R.sub.4 is ##STR11## and the other is primary or secondary C.sub.1-6 alkyl not containing an asymmetric carbon atom, C.sub.3-6 cycloalkyl or phenyl-(CH.sub.2).sub.m -, wherein R.sub.7 is hydrogen, C.sub.1-3 alkyl, n-butyl, i-butyl, t-butyl, C.sub.1-3 alkoxy, n-butoxy, i-butoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R.sub.8 is hydrogen, C.sub.1-3 alkyl, C.sub.1-3 alkoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R.sub.9 is hydrogen, C.sub.1-2 alkyl, C.sub.1-2 alkoxy, fluoro or chloro, and m is 1, 2 or 3, with the provisos that not more than one of R.sub.7 and R.sub.8 is trifluoromethyl, not more than one of R.sub.7 and R.sub.8 is phenoxy, and not more than one of R.sub.7 and R.sub.8 is benzyloxy, R.sub.5 is hydrogen, C.sub.1-3 alkyl, n-butyl, i-butyl, t-butyl, C.sub.3-6 cycloalkyl, C.sub.1-3 alkoxy, n-butoxy, i-butoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, and R.sub.6 is hydrogen, C.sub.1-3 alkyl, C.sub.1-3 alkoxy, trifluoromethyl, fluoro, chloro, phenoxy, or benzyloxy, with the provisos that not more than one of R.sub.5 and R.sub.6 is trifluoromethyl, not more than one of R.sub.5 and R.sub.6 is phenoxy, and not more than one of R.sub.5 and R.sub.6 is benzyloxy, R.sub.10 is C.sub.1-6 alkyl, each X is chloro or bromo, and each X.sup..crclbar. is chloride or bromide.

  合成式为##STR1##化合物的过程，包括以下步骤：(i)将式为##STR2##的化合物与草酰氯或草酰溴反应，形成相应的式为##STR3##的化合物；(ii)将式为##STR4##的化合物与式为##STR5##的化合物反应，形成相应的式为##STR6##的化合物；(iii)水解式为##STR7##的化合物，获得相应的式为##STR8##的化合物。使用式为##STR9##的化合物合成式为##STR10##的化合物，并使用式为VII的中间体直接合成式为II的化合物，其中R.sub.1为C.sub.1-3烷基，苯基或苯基取代物，每个取代基都是独立的C.sub.1-3烷基，C.sub.1-3烷氧基，氟，氯，溴或硝基（最多两个硝基），R.sub.1b为苯基或苯基取代物，每个取代基都是独立的C.sub.1-3烷基，C.sub.1-3烷氧基，氟，氯，溴或硝基（最多两个硝基），R.sub.2为C.sub.1-3烷基，R.sub.3和R.sub.4中的一个为##STR11##，另一个为不含不对称碳原子的一级或二级C.sub.1-6烷基，C.sub.3-6环烷基或苯基-(CH.sub.2).sub.m-，其中R.sub.7为氢，C.sub.1-3烷基，正丁基，异丁基，叔丁基，C.sub.1-3烷氧基，正丁氧基，异丁氧基，三氟甲基，氟，氯，苯氧基或苄氧基，R.sub.8为氢，C.sub.1-3烷基，C.sub.1-3烷氧基，三氟甲基，氟，氯，苯氧基或苄氧基，R.sub.9为氢，C.sub.1-2烷基，C.sub.1-2烷氧基，氟或氯，m为1、2或3，条件是R.sub.7和R.sub.8中最多只有一个是三氟甲基，最多只有一个是苯氧基，最多只有一个是苄氧基，R.sub.5为氢，C.sub.1-3烷基，正丁基，异丁基，叔丁基，C.sub.3-6环烷基，C.sub.1-3烷氧基，正丁氧基，异丁氧基，三氟甲基，氟，氯，苯氧基或苄氧基，R.sub.6为氢，C.sub.1-3烷基，C.sub.1-3烷氧基，三氟甲基，氟，氯，苯氧基或苄氧基，条件是R.sub.5和R.sub.6中最多只有一个是三氟甲基，最多只有一个是苯氧基，最多只有一个是苄氧基，R.sub.10为C.sub.1-6烷基，每个X为氯或溴，每个X.sup..crclbar.为氯化物或溴化物。
• A Stereospecific Synthesis of (<i>E, Z</i>)-α, β-γ, δ-Diunsaturated Aldehydes, Ketones, and Esters Using the<i>Benary</i>Reaction
  作者：Ferdinand Näf、René Decorzant

  DOI：10.1002/hlca.19740570507

  日期：1974.7.17

  The reaction between (Z)-1-alkenyllithium and (E)-β-(N, N-dialkylamino)-α, β-alkenals, (E)-β-(N, N-dialkylamino)-α, β-alkenones or (E)-β-(N, N-dialkylamino)-α, β-alkenoic esters yields mainly (E, Z)-α, β-γ, δ-diunsaturated aldehydes, ketones, or esters and is therefore highly stereospecific.

  （Z）-1-烯基锂与（E）-β-（N，N-二烷基氨基）-α，β-烯醛，（E）-β-（N，N-二烷基氨基）-α，β-烯酮之间的反应或（E）-β-（N，N-二烷基氨基）-α，β-链烯酸酯主要产生（E，Z）-α，β-γ，δ-二不饱和醛，酮或酯，因此具有高度立体选择性。